NP-MRD: Showing NP-Card for Denudatine (NP0050787)

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Record Information

Version

2.0

Created at

2022-04-27 22:06:55 UTC

Updated at

2022-04-27 22:06:55 UTC

NP-MRD ID

NP0050787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Denudatine

Description

Denudatine belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Denudatine is found in Aconitum barbatum, Aconitum carmichaelii, Aconitum kusnezoffii, Aconitum nagarum, Aconitum nagarum var.heterotrichum, Delphinium denudatum and Delphinium denudatum Wall. . Denudatine was first documented in 2018 (PMID: 29212360). Based on a literature review a small amount of articles have been published on Denudatine (PMID: 33351595) (PMID: 34080502) (PMID: 31927015) (PMID: 31602894).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200062D          

 25 30  0  0  1  0            999 V2000
    7.4039   -0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7936    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3940    1.1043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5950    0.7899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9817    0.2588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5549   -0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    0.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4889    0.6514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0816    1.2942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6926    0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9448    1.2565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3469    2.0121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1844    1.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9559    2.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3896    3.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.5664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0958   -0.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2942   -0.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8033   -0.6330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6479   -0.7163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0058   -1.4596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9882    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769    1.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1635    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  4 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  6  0  0  0
 16 24  1  1  0  0  0
  3 25  1  1  0  0  0
M  END


  Mrv1652304282200062D          

 25 30  0  0  1  0            999 V2000
    7.4039   -0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7936    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3940    1.1043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5950    0.7899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9817    0.2588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5549   -0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    0.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4889    0.6514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0816    1.2942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6926    0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9448    1.2565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3469    2.0121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1844    1.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9559    2.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3896    3.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.5664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0958   -0.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2942   -0.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8033   -0.6330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6479   -0.7163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0058   -1.4596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9882    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769    1.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1635    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  4 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  6  0  0  0
 16 24  1  1  0  0  0
  3 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CCC[C@]34[C@H]1[C@H](C[C@H]23)[C@@]12CC[C@@H]([C@H](O)[C@@H]41)C(=C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO2/c1-4-23-11-20(3)7-5-8-22-15(20)10-14(18(22)23)21-9-6-13(12(2)19(21)25)16(24)17(21)22/h13-19,24-25H,2,4-11H2,1,3H3/t13-,14+,15-,16+,17-,18-,19-,20+,21+,22+/m1/s1

> <INCHI_KEY>
OVXLNQAYPUEDSI-ZAWREGRRSA-N

> <FORMULA>
C22H33NO2

> <MOLECULAR_WEIGHT>
343.511

> <EXACT_MASS>
343.251129307

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05998231571739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,8R,9R,10S,11R,13R,14S,15S,16R)-7-ethyl-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.8396510840000007

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.723262790973184

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.994385046000637

> <JCHEM_PKA_STRONGEST_BASIC>
10.10361570004719

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
98.09609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,8R,9R,10S,11R,13R,14S,15S,16R)-7-ethyl-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.821  -0.734   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.548   0.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.802   2.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.311   1.474   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.166   0.483   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.236  -0.739   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.553   0.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.379   1.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.486   2.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.626   1.419   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.097   2.345   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.847   3.756   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      13.411   3.608   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.118   5.112   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.927   6.422   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.573   1.057   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.779  -0.329   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.283  -0.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.099  -1.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.676  -1.337   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.344  -2.725   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.445   0.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.215   2.087   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.744   2.355   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.239   2.617   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13   25                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   11                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   20                                                  
CONECT    8    7    9   16   23                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    3                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    8   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22    8                                                       
CONECT   24   16                                                            
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₂

Average Mass

343.5110 Da

Monoisotopic Mass

343.25113 Da

IUPAC Name

(1S,5R,8R,9R,10S,11R,13R,14S,15S,16R)-7-ethyl-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

Traditional Name

(1S,5R,8R,9R,10S,11R,13R,14S,15S,16R)-7-ethyl-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CCC[C@]34[C@H]1[C@H](C[C@H]23)[C@@]12CC[C@@H]([C@H](O)[C@@H]41)C(=C)[C@H]2O

InChI Identifier

InChI=1S/C22H33NO2/c1-4-23-11-20(3)7-5-8-22-15(20)10-14(18(22)23)21-9-6-13(12(2)19(21)25)16(24)17(21)22/h13-19,24-25H,2,4-11H2,1,3H3/t13-,14+,15-,16+,17-,18-,19-,20+,21+,22+/m1/s1

InChI Key

OVXLNQAYPUEDSI-ZAWREGRRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum barbatum	LOTUS Database	35616633
Aconitum carmichaelii	LOTUS Database	35616633
Aconitum kusnezoffii	LOTUS Database	35616633
Aconitum nagarum	LOTUS Database	35616633
Aconitum nagarum var.heterotrichum	Plant	KNApSAcK
Delphinium denudatum	Plant	KNApSAcK
Delphinium denudatum Wall.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Amine
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2	ALOGPS
logP	1.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.99	ChemAxon
pKa (Strongest Basic)	10.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.1 m³·mol⁻¹	ChemAxon
Polarizability	40.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001636

Chemspider ID

78434168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92854548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu XY, Wang FP, Qin Y: Synthesis of Three-Dimensionally Fascinating Diterpenoid Alkaloids and Related Diterpenes. Acc Chem Res. 2021 Jan 5;54(1):22-34. doi: 10.1021/acs.accounts.0c00720. Epub 2020 Dec 22. [PubMed:33351595 ]
Liu H, Shao S, Xia H, Wu YZ, Zhu CG, Xu CB, Zhang TT, Guo QL, Shi JG: Denudatine-type diterpenoid alkaloids from an aqueous extract of the lateral root of Aconitum carmichaelii. J Asian Nat Prod Res. 2021 Jul;23(7):615-626. doi: 10.1080/10286020.2021.1931141. Epub 2021 Jun 3. [PubMed:34080502 ]
Jiang GY, Qin LL, Gao F, Huang S, Zhou XL: Fifteen new diterpenoid alkaloids from the roots of Aconitum kirinense Nakai. Fitoterapia. 2020 Mar;141:104477. doi: 10.1016/j.fitote.2020.104477. Epub 2020 Jan 10. [PubMed:31927015 ]
Yang B, Han Y, Zhang QY, Dong H, Sun H, Wang XJ: [Study on absorbed components of Aconitum kusnezoffii under Yunnan Baiyao compatibility in effect of activating blood circulation and removing blood stasis]. Zhongguo Zhong Yao Za Zhi. 2019 Aug;44(15):3349-3357. doi: 10.19540/j.cnki.cjcmm.20190711.202. [PubMed:31602894 ]
Samanbay A, Zhao B, Aisa HA: A new denudatine type C20-diterpenoid alkaloid from Aconitum sinchiangense W. T. Wang. Nat Prod Res. 2018 Oct;32(19):2319-2324. doi: 10.1080/14786419.2017.1410814. Epub 2017 Dec 6. [PubMed:29212360 ]

Showing NP-Card for Denudatine (NP0050787)

MOL for NP0050787 (Denudatine)

3D MOL for NP0050787 (Denudatine)

3D SDF for NP0050787 (Denudatine)

3D-SDF for NP0050787 (Denudatine)

PDB for NP0050787 (Denudatine)

3D PDB for NP0050787 (Denudatine)

SMILES for NP0050787 (Denudatine)

INCHI for NP0050787 (Denudatine)

Structure for NP0050787 (Denudatine)

3D Structure for NP0050787 (Denudatine)